Acetic Acid → 6-fluoro-5-methyl-1H-indole

HRID 1674590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674590
C(OC(=O)[CH:10]([C:22]#[N:23])[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[CH:13][C:12]=1[N+]([O-])=O)C1C=CC=CC=1.C(O)(=O)C.O.[H][H]>C(O)C.[C].[Pd]>[F:18][C:14]1[CH:13]=[C:12]2[C:11]([CH:10]=[CH:22][NH:23]2)=[CH:16][C:15]=1[CH3:17]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 962Water2×HCID 58437495Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 27746116-fluoro-5-methyl-1H-indoleAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g).

Aufarbeitung

  1. customThe insoluble material was removed by filtration
  2. extractionthis filtrate was extracted with diethyl ether
  3. washThis organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

Quellen und Nachweise

ORD-Eintrag
ord-d972bf12108e403aa7207bcad86c34ea
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003647B2

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